In April of this year, I dived full on into trying to start a freelance writing career on Upwork. After five months, here’s what I learned.

In my view, being a freelance writer on Upwork is enormously inefficient when it comes to time and money, at least for beginners like myself.

I think that in order to succeed as a freelance writer, you really ought to:

  • be a naturally fast worker
  • work with a moderate balance between quality and quantity
  • and be actually decent at juggling many tasks (even though multitasking has been proven to be highly inefficient).

You probably won’t do very well if…

  • you’re a perfectionist
  • or if you do your best work when you’re highly focused.

When you’re a freelance writer, there are many threats to your free time. And as we all know, time is money. The causes boil down to two factors.

First, many of the prospective clients on Upwork don’t know exactly what they want. This is problematic because it makes it hard to write a decent proposal—how can you give them the most relevant information about yourself if you don’t know what they’re looking for? If you end up actually talking with the prospect, you basically spend a lot of time communicating with them to learn the details of their project. These are needed to turn out a good piece of work. From there, you might not even get the job. I’ve spent anywhere from 2-4 hours communicating with a individual clients with nothing to show for it. With my sales and management experience, you can bet that it has more to do with their lack of commitment to seeing the project through than it has to do with my people skills.

The second factor that threatens your free time is the need to apply to many gigs. You need to do this because the likelihood of you getting a paying gig isn’t that high. It could be for any number of reasons, including the client’s perception of your fit for the gig, the effectiveness of your proposal, etc. Sometimes—in my experience, many times—the client is just testing the waters and hasn’t committed to hiring anyone.

If you’re spending so much time applying to gigs and getting to know a prospective client, you’d hope that the pay when you finally land a gig is decent. Sadly, that isn’t true.

The truth is that most gigs on Upwork don’t pay very well. In my experience, it’s very rare to find a client who pays well by American standards. There are lots of wantrepreneurs (wanna-be entrepreneurs) who are trying to build a tiny business (less than $100,000 in annual revenue). They want sellable work at silly-low prices. For instance, I’ve seen a steady stream of wantrepreneurs who want to pay a paltry $150 for an eBook that take a decent writer no less than 2-3 days of work. After taxes and Upwork fees, that’s something like $75, which works out to an optimistic $3 an hour. Babysitters get paid more than that. I don’t know any American college graduate who can live on that kind of wage.

It’s even more rare to get a client who has a decent idea of what they want you to deliver. If you ever find a client who has a fair amount of samples and research to show you, that’s a good client and you should be doing your best to secure their business. As with most anything in life, outputs of a system are defined by the inputs. Your work is the output. The input is the communication between you and your prospective client. In order for you to create work that meets a clients’ expectations (high-quality output), the inputs need to be high-quality as well.


When it comes to replacing a living-wage income, I don’t think freelance work is for me. I’m not particularly good at concurrently juggling a number of gigs, and I end up spending most of my free time applying to more jobs. And I find myself having trouble finding work-life balance. One big reason is because of the way Upwork encourages freelancers to reply to clients’ job invitations within 24 hours. A lot of the time, I get sent invitations on Friday night or Saturday, which means I have to reply to them over the weekend. Declining them is easy, but if you like the job you have to send a proposal, which means you’re working on the weekend.

Although I have my qualms about working a traditional job in a poorly managed organization (which describes the majority of jobs available), at the end of the day you’ve got a steady paycheck. I think that my feelings about freelance work would be more forgiving if I had transitioned into it while I had full-time employment. And to be fair, I’ve read that it could take 12 to 16 months for a freelance career to take off. I’ve never been very patient, especially when I’m not being compensated for suffering fools. Instead, I now look at it less as a primary source of income and more as a supplement, and I only take on jobs that meet my requirements, which are simple: a well-defined gig at an acceptable pay rate. So, ultimately, I’m not deriding freelance writing completely. It’s just not an appropriate venture at this stage in my life.

Do you think you’d like to be a freelance writer on Upwork? What’s your experience with freelance writing? Share your thoughts in the comments!